US6200932B1 - Phenyl-substituted cyclic ketoenol - Google Patents

Phenyl-substituted cyclic ketoenol Download PDF

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US6200932B1
US6200932B1 US09/230,750 US23075099A US6200932B1 US 6200932 B1 US6200932 B1 US 6200932B1 US 23075099 A US23075099 A US 23075099A US 6200932 B1 US6200932 B1 US 6200932B1
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alkyl
substituted
unsubstituted
alkoxy
fluorine
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Reiner Fischer
Udo Schneider
Peter Dahmen
Markus Dollinger
Christoph Erdelen
Ulrike Wachendorff-Neumann
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

Definitions

  • the invention relates to novel phenyl-substituted cyclic ketoenols, to a plurality of processes for their preparation and to their use as pesticides and herbicides.
  • EP 668 267 having herbicidal, acaricidal and insecticidal action are known.
  • X represents halogen, alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkenyl, halogenoalkoxy, halogenoalkenyloxy, nitro, cyano or represents phenyl, phenoxy, phenylthio, benzyloxy or benzylthio, each of which is optionally substituted,
  • Y represents hydrogen, halogen alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkenyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,
  • Z represents halogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, alkoxy, alkenyloxy, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,
  • n 0, 1, 2 or 3
  • A represents hydrogen, represents alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which is optionally substituted by halogen, represents saturated or unsaturated cycloalkyl which is optionally substituted and in which optionally at least one ring atom is replaced by a heteroatom, or represents aryl, arylalkyl or hetaryl, each of which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, cyano or nitro and which may optionally be substituted by substituted phenoxy, benzyloxy or hetaryloxy,
  • B represents hydrogen or represents alkyl or alkoxyalkyl, each of which is optionally substituted by halogen, or
  • a and B together with the linking carbon atom represent a saturated or unsaturated, unsubstituted or substituted ring which optionally contains a heteroatom
  • G represents hydrogen (a) or represents one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulphur
  • M represents oxygen or sulphur
  • R 1 represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, each of which is optionally substituted by halogen, or represents optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom or represents phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, each of which is optionally substituted,
  • R 2 represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each of which is optionally substituted by halogen, or represents cycloalkyl, phenyl or benzyl, each of which is optionally substituted,
  • R 3 , R 4 and R 5 independently of one another each represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, each of which is optionally substituted by halogen, or represent phenyl, benzyl, phenoxy or phenylthio, each of which is optionally substituted, and
  • R 6 and R 7 independently of one another each represent hydrogen, represent alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, each of which is optionally substituted by halogen, represent optionally substituted phenyl, represent optionally substituted benzyl, or together with the linking N atom represent an optionally by oxygen- or sulphur-containing ring.
  • the compounds of the formula (I) can be present as geometric and/or optical isomers or isomer mixtures of different -composition which can be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and compositions comprising them form part of the subject matter of the present invention. In the following, for simplicity, however, compounds of the formula (I) are always referred to, although both pure compounds and, if appropriate, mixtures having different proportions of isomeric compounds are intended.
  • A, B, X, Y, Z and n are each as defined above
  • A, B, X, Y, Z and n are each as defined above and
  • R 8 represents alkyl (preferably C 1 -C 6 -alkyl)
  • R 1 is as defined above and
  • Hal represents halogen (in particular chlorine or bromine)
  • R 1 is as defined above
  • R 2 and M are each as defined above,
  • R 3 is as defined above
  • R 4 and R 5 are each as defined above and
  • Hal represents halogen (in particular chlorine or bromine),
  • Me represents a mono- or divalent metal (preferably an alkali metal or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium),
  • t represents the number 1 or 2
  • R 10 , R 11 , R 12 independently of one another each represent hydrogen or alkyl (preferably C 1 -C 8 -alkyl),
  • R 6 and R 7 are each as defined above,
  • the compounds of the formulae (I-a) according to the invention are important intermediates for preparing the compounds of the formulae (I) according to the invention in which G represents one of the groups b), c), d), e), f) or g).
  • novel compounds of the formula (I) have very good activity as pesticides, preferably as insecticides, acaricides and herbicides.
  • X preferably represents halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -halogenoalkyl, C 2 -C 6 -halogenoalkenyl, C 1 -C 6 -halogenoalkoxy, C 3 -C 6 -halogenoalkenyloxy, nitro, cyano or represents phenyl, phenoxy, phenylthio, benzyloxy or benzylthio, each of which is optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -
  • Y preferably represents hydrogen, halogen, C-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -halogenoalkyl, C 2 -C 6 -halogenoalkenyl, C 1 -C 6 -halogenoalkoxy, C 3 -C 6 -halogenoalkenyloxy, nitro or cyano,
  • Z preferably represents halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 1 -C 6 -halogenoalkyl, C 2 -C 6 -halogenoalkenyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 1 -C 6 -halogenoalkoxy, C 3 -C 6 -halogenoalkenyloxy, nitro or cyano,
  • n preferably represents 0, 1, 2 or 3,
  • A preferably represents hydrogen or represents C 1 -C 12 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkinyl, C 1 -C 10 -alkoxy-C 1 -C 8 -alkyl, poly-C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl or C 1 -C 10 -alkylthio-C 1 -C 6 -alkyl, each of which is optionally substituted by halogen, represents optionally halogen-, C 1 -C 6 -alkyl- or C 1 -C 6 -alkoxy-substituted C 3 -C 8 -cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur or represents phenyl or naphthyl, hetaryl having 5 to 6 ring atoms, preferably furanyl, pyridyl, imidazolyl, triazolyl
  • B preferably represents hydrogen or represents C 1 -C 12 -alkyl or C 1 -C 8 -alkoxy-C 1 -C 6 -alkyl, each of which is optionally substituted by halogen, or
  • A, B and the linking carbon atom preferably represent saturated or unsaturated C 3 -C 10 -cycloalkyl (in particular C 5 -C 8 -cycloalkyl), in which optionally one methylene group is replaced by oxygen or sulphur and which is optionally mono- or polysubstituted by C 1 -C 8 -alkyl, C 3 -C 10 -cycloalkyl, C 1 -C 8 -halogenoalkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, halogen or phenyl or
  • A, B and the linking carbon atom preferably represent C 5 -C 8 -cycloalkyl or C 5 -C 8 -cycloalkenyl, in which two substituents together with the linking carbon atoms represent C 5 -C 6 -alkanediyl, C 5 -C 6 -alkenediyl or C 6 -alkanedienediyl, each of which is optionally substituted by C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or halogen and in which optionally one methylene group is replaced by oxygen or sulphur.
  • G preferably represents hydrogen (a) or represents one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulphur
  • M represents oxygen or sulphur.
  • R 1 preferably represents C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -alkylthio-C 1 -C 8 -alkyl or poly-C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, each of which is optionally substituted by halogen, or represents optionally halogen-, C 1 -C 6 -alkyl- or C 1 -C 6 -alkoxy-substituted C 3 -C 8 -cycloalkyl, in which optionally at least one methylene group is replaced by oxygen or sulphur,
  • R 2 preferably represents C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl or poly-C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl, each of which is optionally substituted by halogen,
  • R 3 preferably represents optionally halogen-substituted C 1 -C 8 -alkyl or represents phenyl or benzyl, each of which is optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, cyano or nitro.
  • R 4 and R 5 independently of one another each preferably represent C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylamino, di-(C 1 -C 8 -alkyl)amino, C 1 -C 8 -alkylthio, C 2 -C 8 -alkenylthio or C 3 -C 7 -cycloalkylthio, each of which is optionally substituted by halogen, or represent phenyl, phenoxy or phenylthio, each of which is optionally substituted by halogen, nitro, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -halogenoalkylthio, C 1 -C 4 -alkyl or C 1 -C 4 -halogenoalkyl.
  • R 6 and R 7 independently of one another each preferably represent hydrogen, represent C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -alkoxy, C 3 -C 8 -alkenyl or C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, each of which is optionally substituted by halogen, represent optionally halogen-, C 1 -C 8 -halogenoalkyl-, C 1 -C 8 -alkyl- or C 1 -C 8 -alkoxy-substituted phenyl, optionally halogen-, C 1 -C 8 -alkyl-, C 1 -C 8 -halogenoalkyl- or C 1 -C 8 -alkoxy-substituted benzyl or together represent a C 3 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulph
  • X particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, nitro, cyano or represents phenyl or benzyloxy, each of which is optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -halogenoalkyl, C 1 -C 2 -halogenoalkoxy, nitro or cyano.
  • Y particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 3 -C 4 -alkenyloxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, nitro or cyano.
  • Z particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, nitro or cyano.
  • n particularly preferably represents 0, 1, 2 or 3 (in particular represents 0, 1 or 2).
  • B particularly preferably represents hydrogen or represents C 1 -C 10 -alkyl or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, each of which is optionally substituted by fluorine or chlorine, or
  • A, B and the linking carbon atom particularly preferably represent saturated or unsaturated C 5 -C 8 -cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur and which is optionally substituted by C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 3 -halogenoalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, fluorine, chlorine or phenyl or
  • A, B and the linking carbon atom particularly preferably represent C 5 -C 6 -cycloalkyl or C 5 -C 6 -cycloalkenyl in which two substituents together with the linking carbon atoms represent C 5 -C 6 -alkanediyl, C 5 -C 6 -alkenediyl or C 6 -alkanedienediyl, each of which is optionally substituted by C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy, fluorine, chlorine or bromine, and in which optionally one methylene group is replaced by oxygen or sulphur.
  • G particularly preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulphur
  • M represents oxygen or sulphur.
  • R 1 particularly preferably represents C 1 -C 16 -alkyl, C 2 -C 16 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl or poly-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, each of which is optionally substituted by fluorine or chlorine, or optionally fluorine-, chlorine-, C 1 -C 5 -alkyl- or C 1 -C 5 -alkoxy-substituted C 3 -C 7 -cycloalkyl in which optionally one or two not directly adjacent methylene groups are replaced by oxygen or sulphur,
  • pyrazolyl particularly preferably represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally substituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl,
  • pyridyloxy-C 1 -C 5 -alkyl particularly preferably represents pyridyloxy-C 1 -C 5 -alkyl, pyrimidyloxy-C 1 -C 5 -alkyl or thiazolyloxy-C 1 -C 5 -alkyl, each of which is optionally substituted by -fluorine, chlorine, bromine, amino or C 1 -C 4 -alkyl.
  • R 2 particularly preferably represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl or poly-C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl, each of which is optionally substituted by fluorine or chlorine,
  • phenyl or benzyl each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -halogenoalkyl or C 1 -C 3 -halogenoalkoxy.
  • R 3 particularly preferably represents optionally fluorine- or chlorine-substituted C 1 -C 6 -alkyl or represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, bromine, C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy, C 1 -C 3 -halogenoalkyl, C 1 -C 3 -halogenoalkoxy, cyano or nitro,
  • R 4 and R 5 independently of one another each particularly preferably represent C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di-(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylthio, C 3 -C 4 -alkenylthio or C 3 -C 6 -cycloalkylthio, each of which is optionally substituted by fluorine or chlorine, or represent phenyl, phenoxy or phenylthio, each of which is optionally substituted by fluorine, chlorine, bromine, vitro, cyano, C 1 -C 3 -alkoxy, C 1 -C 3 -halogenoalkoxy, C 1 -C 3 -alkylthio, C 1 -C 3 -halogenoalkylthio, C 1 -C 3 -alkyl or C 1 -C 3 -halogen
  • R 6 and R 7 independently of one another each particularly preferably represent hydrogen, represent C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyl or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, each of which is optionally substituted by halogen, represent optionally halogen-, C 1 -C 5 -halogenoalkyl-, C 1 -C 5 -alkyl- or C 1 -C 5 -alkoxy-substituted phenyl, represent optionally halogen-, C 1 -C 5 -alkyl-, C 1 -C 5 -halogenoalkyl- or C 1 -C 5 -alkoxy-substituted benzyl, or together represent a C 3 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or
  • X very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, methoxy, ethoxy, propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano.
  • Y very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, propoxy, iso-propoxy, allyloxy, methallyloxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano.
  • Z very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, difluoromethoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano.
  • n very particularly preferably represents 0, 1, 2 or 3 (in particular represents 0, 1 or 2, specifically represents 0 or 1).
  • B very particularly preferably represents hydrogen or represents C 1 -C 8 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, each of which is optionally substituted by fluorine, or
  • A, B and the linking carbon atom very particularly preferably represent saturated or unsaturated C 5 -C 6 -cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur and which is optionally substituted by methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, fluorine, chlorine or phenyl or
  • A, B and the linking carbon atom very particularly preferably represent C 5 -C 6 -cycloalkyl or C 5 -C 6 -cycloalkenyl in which two substituents together with the linking carbon atoms represent C 5 -C 6 -alkanediyl, C 5 -C 6 -alkenediyl or C 6 -alkanedienediyl.
  • G very particularly preferably represents hydrogen (a) or represents one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulphur
  • M represents oxygen or sulphur
  • R 1 very particularly preferably represents C 1 -C 14 -alkyl, C 2 -C 14 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 6 -alkyl or poly-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, each of which is optionally substituted by fluorine or chlorine, or optionally fluorine-, chlorine-, methyl-, ethyl-, propyl-, i-propyl-, butyl-, i-butyl-, tert-butyl-, methoxy-, ethoxy-, propoxy- or iso-propoxy-substituted C 3 -C 6 -cycloalkyl in which optionally one or two not directly adjacent methylene groups are replaced by oxygen or sulphur,
  • very particularly preferably represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-, methylsulphonyl- or ethylsulphonyl-substituted phenyl,
  • very particularly preferably represents optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted benzyl,
  • pyridyloxy-C 1 -C 4 -alkyl very particularly preferably represents pyridyloxy-C 1 -C 4 -alkyl, pyrimidyloxy-C 1 -C 4 -alkyl or thiazolyloxy-C 1 -C 4 -alkyl, each of which is optionally substituted by fluorine, chlorine, amino, methyl or ethyl.
  • R 2 very particularly preferably represents C 1 -C 14 -alkyl, C 2 -C 14 -alkenyl, C 1 -C 4 -alkoxy-C 2 -C 6 -alkyl or poly-C 1 -C 4 -alkoxy-C 2 -C 6 -alkyl, each of which is optionally substituted by fluorine or chlorine,
  • phenyl or benzyl each of which is optionally substituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy.
  • R 3 very particularly preferably represents methyl, ethyl, propyl, isopropyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, iso-propyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
  • R 4 and R 5 independently of one another each very particularly preferably represent C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkylthio, each of which is optionally substituted by fluorine or chlorine, or represent phenyl, phenoxy or phenylthio, each of which is optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 2 -alkoxy, C 1 -C 2 -fluoroalkoxy, C 1 -C 2 -alkylthio, C 1 -C 2 -fluoroalkylthio or C 1 -C 3 -alkyl.
  • R 6 and R 7 independently of one another each very particularly preferably represent hydrogen, represent C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 3 -C 4 -alkenyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, each of which is optionally substituted by fluorine or chlorine, represent optionally fluorine-, chlorine-, bromine-, C 1 -C 4 -halogenoalkyl-, C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted phenyl, represent optionally fluorine-, chlorine-, bromine-, C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkyl- or C 1 -C 4 -alkoxy-substituted benzyl, or together represent a C 5 -C 6 -al
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can, as far as possible, in each case be straight-chain or branched, also in combination with heteroatoms, such as, for example, in alkoxy.
  • Optionally substituted radicals can be mono- or polysubstituted, it being possible in the case of polysubstitution for the substituents to be identical or different.
  • A, B, D, X, Y, Z, R 8 and n are each as defined above,
  • acylamino acid esters of formula (II) are obtained, for example, when amino acid derivatives of the formula (XII)
  • A, B and R 8 are each as defined above
  • X, Y, Z and n are each as defined above and
  • Hal represents chlorine or bromine
  • amino acid esters of the formula (XII) are obtained, for example, when nitrocarboxylic esters of the formula (XIV)
  • A, B and R 8 are each as defined above
  • a hydrogenation catalyst such as, for example, Raney cobalt or Raney nickel, palladium or platinum (for example on a carbon support), if appropriate in the presence of a diluent, such as, for example, methanol or ethanol, at temperatures between ⁇ 20° C. and +200° C., preferably between 0° C. and 150° C., and at pressures between 1 bar and 300 bar, preferably between 10 bar and 200 bar (cf. Preparation Examples).
  • a hydrogenation catalyst such as, for example, Raney cobalt or Raney nickel, palladium or platinum (for example on a carbon support)
  • a diluent such as, for example, methanol or ethanol
  • acylamino esters of the formula (II) are obtained, for example, when amino acid derivatives of the formula (XV)
  • A, B, X, Y, Z and n are each as defined above
  • the compounds of the formula (XV) are novel, but they can be prepared using the method of a known process (Polniaszek, Stevens, J. Org. Chem. 51, 3023-3027, 1986).
  • amino acid derivatives of the formula (XV) are obtained, for example, when acyl amino alcohols of the formula (XVI)
  • A, B, X, Y, Z and n are each as defined above,
  • Swern Polyaszek, Stevens, J. Org. Chem. 51, 3023-3027, 1986; Omura, Swem, Tetrahedron 34, 1951; 1978.
  • acylamino alcohols of the formula (XVI) are obtained, for example, when 5-amino-5-hydroxymethyl-1,3-dioxanes of the formula (XVII)
  • a and B are each as defined above
  • X, Y, Z and n are each as defined above and
  • Hal represents chlorine or bromine
  • amino alcohols of the formula (XVII) are obtained, for example, when nitro alcohols of the formula (XVIII)
  • a and B are each as defined above
  • a hydrogenation catalyst such as, for example, Raney cobalt or Raney nickel, palladium or platinum (for example on a carbon support), if appropriate in the presence of a diluent, such as, for example methanol or ethanol, at temperatures between ⁇ 20° C. and +200° C., preferably between 0° C. and 150° C., and at pressures between 1 bar and 300 bar, preferably between 10 bar and 200 bar (cf. Preparation Examples).
  • a hydrogenation catalyst such as, for example, Raney cobalt or Raney nickel, palladium or platinum (for example on a carbon support)
  • a diluent such as, for example methanol or ethanol
  • a and B are as defined above
  • the acyl halides of the formula (III), carboxylic anhydrides of the formula. (IV), chloroformic esters or chloroformic thioesters of the formula (V), chloromonothioformic esters or chlorodithioformic esters of the formula (VI), sulphonyl chlorides of the formula (VII), phosphorus compounds of the formula (VIII) and metal hydroxides, metal alkoxides or amines of the formula (IX) and (X) and carbamoyl chlorides of the formula (XI) which are furthermore required as starting materials for carrying out the processes (B), (C), (D), (E), (F), (G) and (H) according to the invention are generally known compounds of organic or inorganic chemistry.
  • the process (A) is characterized in that compounds of the formula (II) in which A, B, X, Y, Z, n and R 8 are each as defined above are subjected to an intramolecular condensation in the presence of a base.
  • Suitable diluents for the process (A) according to the invention are all inert organic solvents. Preference is given to using hydrocarbons, such as toluene and xylene, furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, furthermore polar solvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, and also alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tert-butanol.
  • hydrocarbons such as toluene and xylene
  • ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether
  • furthermore polar solvents such as dimethyl
  • all customary proton acceptors can be used as base (deprotonating agent).
  • base deprotonating agent
  • alkali metals such as sodium or potassium may be used.
  • Suitable for use are also alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and furthermore also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide.
  • reaction temperatures can be varied within a relatively wide range.
  • the reaction is carried out at temperatures between 0° C. and 250° C., preferably between 50° C. and 150° C.
  • the process (A) according to the invention is generally carried out under atmospheric pressure.
  • reaction components of the formula (II) and the deprotonating bases are generally employed in approximately equimolar to double-equimolar amounts. However, it is also possible to employ a relatively large excess (up to 3 mol) of one or the other component.
  • the process (B ⁇ ) is characterized in that compounds of the formula (I-a) are reacted with carbonyl halides of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Suitable diluents for the process (Box) according to the invention are all solvents which are inert towards the acyl halides.
  • hydrocarbons such as benzine, benzene, toluene, xylene and tetraline
  • halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene
  • ketones such as acetone and methyl isopropyl ketone
  • nitriles such as acetonitrile
  • furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane
  • carboxylic esters such as ethyl acetate, and also strongly polar solvents such as dimethyl sulphoxide and sulpholane.
  • the stability of the acyl halide hydrolysis permitting, the reaction can also be carried out in the presence of water
  • Suitable acid binders for the reaction according to the process (BaX) according to the invention are all customary acid acceptors. Preference is given to using tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig-Base and N,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such as magnesium oxide and calcium oxide, moreover alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate and also alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig-Bas
  • the reaction temperatures can be varied within a relatively wide range.
  • the reaction is carried out at temperatures between ⁇ 20° C. and +150° C., preferably between 0° C. and 100° C.
  • the starting materials of the formula (I-a) and the carbonyl halide of the formula (f) are generally employed in each case in approximately equivalent amounts. However, it is also possible to employ a relatively large excess (up to 5 mol) of the carbonyl halide. Work-up is carried out by customary methods.
  • the process (B ⁇ ) is characterized in that compounds of the formula (I-a) are reacted with carboxylic anhydrides of the formula (IV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Preferred diluents for the process (BB) according to the invention are those diluents which are also preferred when using acyl halides. Otherwise, a carboxylic anhydride which is employed in excess can simultaneously act as a diluent.
  • Acid binders which may be added in the process (BB) are preferably those acid binders which are also preferred when using acyl halides.
  • reaction temperatures in the process (BB) according to the invention can be varied within a relatively wide range.
  • the reaction is generally carried out between ⁇ 20° C. and +150° C., preferably between 0° C. and 100° C.
  • the starting materials of the formula (I-a) and the carboxylic anhydride of the formula (IV) are generally each employed in approximately equivalent amounts. However, it is also possible to employ a relatively large excess (up to 5 mol) of the carboxylic anhydride. Work-up is carried out by customary methods.
  • diluent and excess carboxylic anhydride and also the carboxylic acid which is formed are removed by distillation or by washing with an organic solvent or with water.
  • the process (C) is characterized in that compounds of the formula (I-a) are reacted with chloroformic esters or chloroformic thiol esters of the formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Suitable acid binders for the reaction according to the process (C) according to the invention are all customary acid acceptors.
  • tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBA, Hünig-Base and N,N-dimethylaniline
  • alkaline earth metal oxides such as magnesium oxide and calcium oxide
  • alkali metal and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate and also alkali metal hydroxides such
  • Suitable diluents for the process (C) according to the invention are all solvents which are inert towards the chloroformic esters or chloroformic thiol esters.
  • hydrocarbons such as benzine, benzene, toluene, xylene and tetraline
  • halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene
  • ketones such as acetone and methyl isopropyl ketone
  • nitrites such as acetonitrile
  • furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane
  • carboxylic esters such as ethyl acetate
  • strongly polar solvents such as dimethyl sulphoxide and sulpholane.
  • reaction temperatures can be varied within a relatively wide range. If the reaction is carried out in the presence of a diluent and an acid binder, the reaction temperatures are generally between ⁇ 20° C. and +100° C., preferably between 0° C. and 50° C.
  • the process (C) according to the invention is generally carried out under atmospheric pressure.
  • the starting materials of the formula (I-a) and the appropriate chloroformic ester or chloroformic thiol ester of the formula (V) are generally each employed in approximately equivalent amounts. However, it is also possible to employ a relatively large excess (up to 2 mol) of one or the other component. Work-up is carried out by customary methods. In general, precipitated salts are removed and the reaction mixture that remains is concentrated by removing the diluent under reduced pressure.
  • the process (D) according to the invention is characterized in that compounds of the formula (I-a) are reacted with compounds of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • Diluents which may be added, if appropriate, are all inert polar organic solvents, such as ethers, nitrites, ketones, carboxylic esters, amides, sulphones, sulphoxides, but also halogenoalkanes.
  • the enolate salt of the compounds of the formula (I-a) is prepared by addition of strong deprotonating agents such as, for example, sodium hydride or potassium tert-butoxide, the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as, for example, sodium hydride or potassium tert-butoxide
  • acid binders customary inorganic or organic bases are suitable; sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamnine may be mentioned by way of example.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods.
  • the process (E) according to the invention is characterized in that compounds of the formula (I-a) are reacted with sulphonyl chlorides of the formula (VII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Diluents which may be added, if appropriate, are all inert polar organic solvents, such as ethers, amides, ketones, carboxylic esters, nitriles, sulphones, sulphoxides or halogenated hydrocarbons such as methylene chloride.
  • the enolate salt of the compounds (I-a) is prepared by addition of strong deprotonating agents (such as, for example, sodium hydride or potassium tert-butoxide), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as, for example, sodium hydride or potassium tert-butoxide
  • acid binders customary inorganic or organic bases are suitable; sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine may be mentioned by way of example.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods.
  • the process (F) according to the invention is characterized in that compounds of the formula (I-a) are in each case reacted with phosphorus compounds of the formula (VIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Diluents which may be added, if appropriate, are all inert polar organic solvents such as ethers, amides, ketones, carboxylic esters, nitriles, alcohols, sulphides, sulphones, sulphoxides, etc.
  • Acid binders which may be added, if appropriate, are customary inorganic or organic bases such as hydroxides, carbonates or amines. Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine may be mentioned by way of example.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods of organic chemistry.
  • the resulting end products are preferably purified by crystallization, chromatographic purification or by so-called “incipient distillation”, i.e. removal of the volatile components under reduced pressure.
  • the process (G) is characterized in that compounds of the formula (I-a) are reacted with metal hydroxides or metal alkoxides of the formula (IX) or amines of the formula (X), if appropriate in the presence of a diluent.
  • Preferred diluents for the process (G) according to the invention are ethers such as tetrahydrofuran, dioxane, diethyl ether or else alcohols such as methanol, ethanol, isopropanol, but also water.
  • the process (G) according to the invention is generally carried out under atmospheric pressure.
  • the reaction temperatures are generally between ⁇ 20° C. and 100° C., preferably between 0° C. and 50° C.
  • Diluents which may be added, if appropriate, are all inert polar organic solvents such as ethers, amides, ketones, carboxylic esters, sulphones, sulphoxides, or halogenated hydrocarbons.
  • the enolate salt of the compound (I-a) is prepared by addition of strong deprotonating agents (such as, for example, sodium hydride or potassium tert-butylate), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as, for example, sodium hydride or potassium tert-butylate
  • acid binders customary inorganic or organic bases are suitable; sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine and pyridine may be mentioned by way of example.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods.
  • the active compounds are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are encountered in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or some stages of development.
  • animal pests preferably arthropods and nematodes, in particular insects and arachnids, which are encountered in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or some stages of development.
  • the abovementioned pests include:
  • Isopoda for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber.
  • Chilopoda for example, Geophilus carpophagus and Scutigera spec.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura for example, Lepisma saccharina.
  • Orthoptera for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Acheta domesticus , Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.
  • Thysanoptera From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.
  • From the order of the Homoptera for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae , Myzus spp., Phorodon humuli, Rhopalosiphum padi , Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae , Pseudococcus spp. and Psylla spp.
  • Hymenoptera From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
  • Acarina for example, Acarus siro , Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora , Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa , Panonychus spp. and Tetranychus spp.
  • the active compounds according to the invention have potent insecticidal and acaricidal activity.
  • insects can be used particularly successfully for controlling plant-damaging insects, such as, for example, against the larvae of the mustard beetle ( Phaedon cochleariae ) or against the larvae of the green rice leaf hopper ( Nephotettix cincticeps ) and against the caterpillars of the diamond-back moth ( Plutella maculipennis ).
  • the active compounds according to the invention can furthermore be used as defoliants, desiccants, haulm-killers and, especially, as weed-killers.
  • weeds in the broadest sense, are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in connection with the following plants:
  • Monocotyledonous crops of the genera Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
  • the compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial cultures, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on lawns, turf and pasture-land, and for the selective control of weeds in annual crops.
  • perennial cultures for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on lawns, turf and pasture-land, and for the selective control of weeds in annual crops.
  • the active compounds according to the invention are highly suitable for the selective control of monocotyledonous weeds in dicotyledonous crops by the pre- and post-emergence methods. They can be employed, for example, very successfully for controlling harmful grasses in cotton or sugar beet.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
  • formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersing agents and/or foam-forming agents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chlor
  • Suitable solid carriers are:
  • ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates; as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as protein
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations in general contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compound according to the invention may be present in its commercial formulations and also in the use forms prepared from these formulations as a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenyl ureas, substances which are prepared by microorganisms, and the like.
  • Particularly suitable compounds for mixtures are, for example, those listed below:
  • dichlorophen diclobutrazol, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine, drazoxolon,
  • fenarimol fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulphamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,
  • copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,
  • mancopper mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulphocarb, methfuroxam, metiram, metsulphovax, myclobutanil,
  • pefurazoate penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamates, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
  • PCNB quintozene
  • tebucanozole tecloftalam, tecnazene, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin, triticonazole,
  • bronopol dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • abamectin abamectin, abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin,
  • Bacillus thuringiensis bendiocarb, benfuracarb, bensultap, beta-cyluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben,
  • edifenphos emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos, etrimphos,
  • fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
  • parathion A parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamdon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,
  • anilides such as, for example, diflufenican and propanil
  • arylcarboxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram
  • aryloxyalkanoic acids such as, for example, 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr
  • aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl
  • azinones such as, for example, chloridazon and norflurazon
  • carbamates such as, for example, chlorpropham, desmedipham, phenmedipham and propham
  • chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor,
  • the active compound according to the invention can furthermore be present in its commercially available formulations and in the use forms prepared from these formulations, as a mixture with synergists.
  • Synergists are compounds which increase the action of the active compounds without it being necessary for the synergist added to be active itself.
  • the active compound content of the use forms prepared from the commercially available formulations can vary within wide limits.
  • the active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
  • the active compound When used against hygiene pests and pests of stored products, the active compound has an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • the active compounds according to the invention are not only active against plant, hygiene and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites), such as ixodid ticks, argasid ticks, scab mites, trombiculid mites, flies (stinging and sucking), parasitic fly larvae, lice, hair lice, bird lice and fleas.
  • animal parasites ectoparasites
  • ixodid ticks such as argasid ticks, scab mites, trombiculid mites, flies (stinging and sucking), parasitic fly larvae, lice, hair lice, bird lice and fleas.
  • Anoplurida for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Nematocerina and Brachycerina for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Chrysomyia spppp.
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Octodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which attack agricultural livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, honey bees, other domestic animals, such as, for example, dogs, cats, cage birds, aquarium fish, and so-called experimental animals such as, for example, hamsters, guinea pigs, rats and mice.
  • arthropods By controlling these arthropods, it is intended to reduce mortality and decreased performance (in meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal keeping is made possible by using the active compounds according to the invention.
  • the active compounds according to the invention are used in a known manner by enteral administration, for example in the form of tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as, for example, by means of injections (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal application, by dermal administration, for example in the form of dipping or bathing, spraying, pouring-on and spotting-on, washing, dusting, and with the aid of shaped articles which comprise active compound, such as collars, ear tags, tail marks, limb bands, halters, marking devices and the like.
  • enteral administration for example in the form of tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration such as, for example, by means of injections (intramuscular
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowables) which comprise the active compounds in an amount of 1 to 80% by weight, either directly or after dilution by a factor of 100 to 10,000, or they may be used in the form of a chemical bath.
  • formulations for example powders, emulsions, flowables
  • insects may be mentioned by way of example and as being preferred, but without any limitation:
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticuliternes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Industrial materials are to be understood as meaning, in the present context, non-live materials such as, preferably, synthetic materials, glues, sizes, paper and board, leather, wood and timber products, and paint.
  • the materials to be very particularly protected against attack by insects are wood and timber products.
  • Wood and timber products which can be protected by the composition according to the invention or mixtures comprising such a composition are to be understood as meaning, for example: construction timber, wooden beams, railway sleepers, bridge components, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wood lagging, windows and doors made of wood, plywood, particle board, joiner's articles, or wood products which, quite generally, are used in the construction of houses or in joinery.
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellent, if appropriate desiccants and UV stabilizers and, if appropriate, colorants and pigments and other processing auxiliaries.
  • the insecticidal compositions or concentrates used for the protection of wood and wooden materials comprise the active compound according to the invention at a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • compositions or concentrates employed depends on the species and the occurrence of the insects and on the medium. The optimum rate of application can be determined upon use in each case by test series. However, in general, it suffices to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • the solvent and/or diluent used is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetting agent.
  • Organochemical solvents which are preferably employed are oily or oil-type solvents having an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C.
  • Substances which are used as such oily and oil-type solvents which have low volatility and are insoluble in water are suitable mineral oils or their aromatic fractions, or mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or alkylbenzene.
  • Substances which are advantageously used are mineral oils with a boiling range of 170 to 220° C., white spirit with a boiling range of 170 to 220° C., spindle oil with a boiling range of 250 to 350° C., petroleum or aromatics of boiling range 160 to 280° C., essence of turpentine and the like.
  • liquid aliphatic hydrocarbons with a boiling range of 180 to 210° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220° C. and/or spindle oil and/or monochloronaphthalene, preferably (x-monochloronaphthalene, are used.
  • organic oily or oil-type solvents of low volatility having an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C. can be partially replaced by organochemical solvents of high or medium volatility, with the proviso that the solvent mixture also has an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C., and that the insecticide/fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organochemical solvent or solvent mixture is replaced by an aliphatic polar organochemical solvent or solvent mixture.
  • Substances which are preferably used are aliphatic organochemical solvents having hydroxyl and/or ester and/or ether groups, such as, for example, glycol ether, esters and the like.
  • the organochemical binders used within the scope of the present invention are the synthetic resins and/or binding drying oils which are known per se and can be diluted with water and/or are soluble or dispersible or emulsifiable in the organochemical solvents employed, in particular binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol resin, hydrocarbon resin, such as indene/coumarone resin, silicone resin, drying vegetable and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.
  • binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol resin, hydrocarbon resin, such as
  • the synthetic resin used as the binder can be employed in the form of an emulsion, dispersion or solution. Up to 10% by weight of bitumen or bituminous substances can also be used as binders. In addition, known colorants, pigments, water repellents, odour-masking substances and inhibitors or anticorrosives per se and the like can also be employed.
  • composition or the concentrate preferably comprises, in accordance with the invention, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil as the organochemical binder.
  • alkyd resins with an oil content of over 45% by weight, preferably 50 to 68% by weight.
  • binder can be replaced by a fixative (mixture) or a plasticizer (mixture).
  • fixative mixture
  • plasticizer mixture
  • additives are intended to prevent volatilization of the active compounds and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of binder employed).
  • the plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate, the phosphoric esters, such as tributyl phosphate, the adipic esters, such as di-(2-ethylhexyl) adipate, the stearates, such as butyl stearate or amyl stearate, the oleates, such as butyl oleate, the glycerol ethers or relatively high-molecular-weight glycol ethers, glycerol esters and p-toluene-sulphonic esters.
  • the phthalic esters such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate
  • the phosphoric esters such as tributyl phosphate
  • the adipic esters such as di-(2-e
  • Fixatives are chemically based on polyvinyl alkyl ethers, such as, for example, polyvinyl methyl ether, or ketones, such as benzophenone or ethylene benzophenone.
  • Particularly suitable as a solvent or diluent is also water, if appropriate as a mixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
  • the ready-to-use compositions can additionally comprise one or more other insecticides and, if appropriate, additionally one or more fungicides.
  • Suitable additional components which may be admixed are, preferably, the insecticides and fungicides mentioned in WO 94/29 268.
  • the compounds mentioned in that document are expressly incorporated into the present application by reference.
  • Very particularly preferred components which may be admixed are insecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron,
  • insecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron,
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluanide, tolylfluanide, 3-iodo-2-propinylbutyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.
  • Example (I-a-7) At 20° C., 3.6 g of the compound of Example (I-a-7) in 50 ml of methanol are admixed with 2 g of sodium methoxide solution and stirred at this temperature for one day. The mixture is then admixed with toluene and evaporated under reduced pressure. Yield: 4.50 g (99% of theory), m.p.: >250° C.
  • Example (II-1) Similarly to Example (II-1), and in accordance with the general preparation procedures, the following compounds of the formula (II) are prepared.
  • the mixture is admixed with n-hexane, the precipitate is filtered off, the filtrate is concentrated using a rotary evaporator and the residue is chromatographed over silica gel using methylene chloride/acetone 2:1.
  • Example (XV-1) Similarly to Example (XV-1), and according to the general procedures, the following compounds of the formula (XV) were prepared.
  • Example XVII-1 45 g (0.25 mol) of the compound of Example XVII-1 are dissolved in 500 ml of anhydrous tetrahydrofuran and admixed with 40 ml of triethylamine, 50 g of misitylene acetyl chloride are added dropwise at 0° C. and the mixture is stirred at room temperature for 1 h. The precipitate is filtered off, the filtrate is concentrated and the residue is chromatographed over silica gel using hexane/ethyl acetate 2:1.
  • Example XVI-1 Similarly to Example XVI-1, and according to the general procedures, the following compounds of the formula XVI were prepared.
  • Tetranychus Test (OP-resistant/dip treatment)
  • Solvent 7.5 parts by weight of dimethylformamide 100 parts by weight of methanol
  • Emulsifier 2.5 parts by weight of alkylaryl polyglycol ether
  • active compound I part by weight of active compound is mixed with the stated amount of emulsifier, and the concentrate is diluted with water with emulsifier-containing water to the desired concentrations.
  • Bean plants Phaseolus vulgaris , which are heavily infested by all stages of the greenhouse red spider mite Tetranychus urticae , are dipped into a preparation of active compound of the desired concentration.
  • the effect in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
  • the compounds of preparation examples I-a-1, I-b-1 and I-c-1 show a kill of ⁇ 98% after 13 d.
  • Phaedon-Larvae Test Solvent 7 parts by weight of dimethylformamide
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves Brassica oleracea
  • Cabbage leaves Brassica oleracea
  • active compound of the desired concentration are treated by being dipped into the preparation of active compound of the desired concentration and are populated with mustard beetle larvae ( Phaedon cochleariae ) while the leaves are still moist.
  • the kill n % is determined. 100% means that all beetle larvae have been killed, 0% means that none of the beetle larvae have been killed.
  • the compounds of preparation examples activity I-a-1, I-b-1, I-b-2-, I-b-3, I-a-4 and I-b-10 show a kill of 100% after 7 days.
  • Plutella Test Solvent 7 parts by weight of dimethylformamide
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves Brassica oleracea
  • Cabbage leaves Brassica oleracea
  • caterpillars of the diamond-back moth Plutella maculipennis
  • the kill n % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
  • the compounds of preparation examples activity I-a-1, I-b-1 and I-c-1 show a kill of 100% after 7 days.
  • Nephotettix Test Solvent 7 parts by weight of dimethylformamide
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Rice seedlings ( Oryzae sativa ) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with larvae of the green rice leaf hopper ( Nephotettix cincticeps ) while the seedlings are still moist.
  • the kill n % is determined. 100% means that all leaf hoppers have been killed; 0% means that none of the leaf hoppers have been killed.
  • the compounds of preparation examples I-a-1, I-b-1, I-c-1, I-b-2, I-c-2, I-a-4, I-b-8 and I-c-4 show a kill of 100% after 6 days.
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves Brassica oleracea
  • Cabbage leaves Brassica oleracea
  • the kill n % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
  • the compounds of preparation examples I-b-2, I-a-4, I-b-8 and I-b-10 show a kill of ⁇ 90% after 7 days.
  • Myzus Test Solvent 7 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage plants Brassica oleracea ) which are heavily infested by peach aphids ( Myzus persicae ) are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill n % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed.
  • the compounds of preparation examples I-a-1, I-a-3, I-b-2, I-c-2, I-a-4 and I-c-4 show a kill of ⁇ 90% after 6 days.

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  • Pest Control & Pesticides (AREA)
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